Parkinson’s disease is a neurodegenerative disorder characterized by several motor symptoms that develop gradually: tremor, bradykinesia, limb rigidity, and gait and balance problems. While there is no cure, levodopa therapy has been shown to mitigate symptoms. A patient on levodopa experiences cycles in the severity of their symptoms, characterized by an ON state—when the drug is active—and an OFF state—when symptoms worsen as the drug wears off. The longitudinal progression of the disease is monitored using episodic assessments performed by trained physicians in the clinic, such as the Unified Parkinson’s Disease Rating Scale (UPDRS). Lately, there has been an effort in the field to develop continuous, objective measures of motor symptoms based on wearable sensors and other remote monitoring devices. In this work, we present an effort towards such a solution that uses a single wearable inertial sensor to automatically assess the postural instability and gait disorder (PIGD) of a Parkinson’s disease patient. Sensor data was collected from two independent studies of subjects performing the UPDRS test and then used to train and validate a convolutional neural network model. Given the typical limited size of such studies we also employed the use of generative adversarial networks to improve the performance of deep-learning models that usually require larger amounts of data for training. We show that for a 2-min walk test, our method’s predicted PIGD scores can be used to identify a patient’s ON/OFF states better than a physician evaluated on the same criteria. This result paves the way for more reliable, continuous tracking of Parkinson’s disease symptoms.